1. Christina Aguilera (2002)
We don’t even know where to start here. Is that a scarf or a top? Are those denim shorts or just..a denim belt? Don’t get us started on that makeup, oy vey.
2. Lil’ Kim (2000)
This look is what happens when super hero costume meets raincoat meets construction meets Lil Kim. We can always count for Lil’ Kim to take it to the limit when it comes to red carpet fashion.
3. Lil’ Mama (2007)
This is just confusing. Why was Lil’ Mama dressed like a big baby? Wait wait wait wait! Was it backwards day??
4. Pamela Anderson and Tommy Lee (1999)
Adventures in bad decisions: the hat wear edition.
5. Rose McGowan (1998)
6. Britney Spears (2002)
All things considered, this Eastern European dominatrix look was pretty tame compared to other outfits Britney performed in over the years.
7. Lady Gaga (2009)
No one can forget the infamous meat dress of 2010, but Gaga’s all-over red lace number was just as memorable.
8. Flavor Flav (1990)
The visual pun between the baseball pajamas and the batman sunglasses takes a second to process, but when you get it, it’s amazing.
9. Steven Tyler (1987)
Truthfully, this is one of the more conservative outfits the Aerosmith lead singer has donned over the years.
10. Will.i.am (2010)
A Black Eyed Pea in black face. There are no words.
11. Paula Abdul (1987)
With that perm and all that glitter, Paula probably fit right in in 1987 - but looking back this look is just a bit crazy. We think it might be the shoulder tassels that throw it over the edge.
12. Fergie (2006)
A little dash of British fashion and a little dash of school girl fancy and where did 65% of her shirt go?
13. Christina Aguilera (2003)
A carnival dancer in Brazil was probably missing her headdress a LOT that year.
14. Outkast (2001)
This picture probably belongs in the “most epic VMA outfits” post but Big Boi’s pants were way too awesome to not include. These two knew swag before swag was swag.
15. Jennifer Lopez (2001)
Jennifer Lopez has always been a fashion trendsetter, but somehow this “jungle pirate gypsy in St. Tropez” trend never quite took off.
16. Gwen Stefani (1998)
Matching your hair to your fuzzy baby blue bra is a move only the most confident of style icons can pull off. That skirt on the other hand? Unforgivable.
17. Nicki Minaj (2011)
Nicki always brings the wacky but this get up definitely fell into the “trying too hard” category. Maybe try ditching the surgical mask next time?
18. Backstreet Boys (1998)
What’s worse than a terrible red carpet outfit? Five terrible red carpet outfits! Thank God the 90s are over.
19. Lenny Kravitz (1993)
You gotta give it up to Lenny: winning a Moonman while dressed as a Moonman is pretty on point.
20. Perez Hilton (2009)